This story appears in the November/December 2017 issue of Playboy. Subscribe

Artist Shepard Fairey prepares to make his biggest statement yet.

In the new Hulu documentary Obey Giant, Shepard Fairey admits that the andre the giant sticker that launched his career as an artist was something of a joke. He was working at a skateboard shop, designing boards and stickers while attending the Rhode Island School of Design, when a friend pointed out an image of the pro wrestler in a local circular. Fairey worked that image into a blotchy black-and-white sticker, added the cryptic phrase andre the giant has a posse and started posting it around town.

The sticker that started it all.

The Giant’s menacing likeness looked vaguely cultish and propagandistic, an effect that was heightened when Fairey later added the word obey to a different version of the design. Soon it became a proto-internet viral sensation. Its proliferation contained a lesson on the power of ambiguity and the effectiveness of exploiting the gap between perception and prejudice—between what a viewer thinks something means and what it could mean. Fairey has mined that gap for the past 28 years.

This November, when the Hulu documentary starts streaming, Fairey will simultaneously open his most ambitious exhibition to date. Called Damaged, a title borrowed from Black Flag’s seminal hardcore album, the Los Angeles show will include more than 150 new paintings, large-scale sculptures, installations, etchings, retired stencils, a newspaper (The Damaged Times) and what Fairey’s website calls “various do-it-yourself tools of empowerment.” It’s something of a cross between an art event and a call to action—an attempt to disrupt what Fairey sees as a rising tide of fear and hate, and a line drawn in the sand from the side of equality and freedom of expression.

“Damaged is an honest diagnosis, but diagnosis is the first step to recognizing and solving problems,” Fairey says. “I think art can be part of the solution, because it can inspire people to look at an issue they might otherwise ignore or reject.”

Characteristically, the nature of the solution Fairey proposes is in the eye of the beholder. His work blends a healthy amount of political symbolism with ambiguous portraiture and referential aesthetics: a woman wrapped in an American-flag hijab; a ragged collage of American World War II propaganda nearly covering another woman’s face; shrill headlines marching around yet another female subject (opposite page, left), her gaze resting just over your head. Fairey’s penchant for blending propagandistic forms—Russian constructivism, in particular—with his stripped-down, red-saturated color palette and intricately layered patterning makes for images that are both iconic and mysterious.

Peace Guard 2 and No Future, two stencil works featured in the show.

There’s something doubly subversive about the way his work embraces printed media, protest posters, Xerox-era technology and other bygone instruments of the counterculture at a moment when the rules of political and cultural expression are being redrawn by digital media.

“The fractured media landscape and the degradation it’s created trouble me,” Fairey says. “I’m emphasizing the importance of searching for quality information and also creating your own media that has content and aesthetic merit.” So is the show a damning critique of our beloved social platforms? Not exactly. “I’m not rejecting social media, but I try to use it in a way that leads people back to more meaningful and less shortsighted ways of creating and consuming,” he says. (The Damaged exhibition will also include the release of work in another medium: new music by Fairey’s band Nøise.)

Despite fame and ever-mounting commissions, Fairey remains committed to the most analog of forms: street art. He still thrives on stickering, painting and wheat-pasting without permission, even after being arrested more than a dozen times.

Perhaps it’s in the indefatigable character of Fairey’s output that we can locate the real takeaway. Despite the grinding challenges of the current moment, the profusion of his work suggests there is still reason to hope.

“Even if I have to take a deep breath and clench my teeth now and then, I’m highly motivated by the possibility to make a difference in the world,” Fairey says. “I’ve always loved the Joe Strummer quote ‘The future is unwritten.’ If you don’t like the way the story is going, start writing it in a different direction.”